When Ayanna Pressley decided to take a shot at a seat on the city council in her adopted hometown of Boston, Mass., she was committed to winning by any means necessary. This meant cashing in her 401(k) retirement plan--earned over 16 years as a Democratic operative in Boston and in Washington for Sen. John Kerry and other lawmakers. With a mother needing regular care, chasing a job that depended entirely on her willingness to, say, shake hands outside Fenway Park, her run was something of a gamble. "I know what it is to live in the margins; I know what it is to feel that your government doesn't reflect you, represent you, or advocate for you," Pressley--whose investment paid off with a win in November 2009--says today. "I was unafraid."

Fearlessness is what it takes for a woman to run for elective office, especially a black woman. In his official proclamation designating March Women's History Month, President Barack Obama noted that America "must correct persisting inequalities" facing women in every sphere of life, such as making less money and having greater family burdens than men.

These inequalities have an impact on representation in the public sphere. Women are only 17 percent of the United States Congress, with the 21 African American, Hispanic and Asian females comprising only 4 percent. The number of black women in Congress has flat-lined since 1992, the so-called "Year of the Woman": There were 11 black women in 1992; 13 in 2002, and only 13 today.

"It is definitely more complicated running for office as a woman," says Andrea Dew Steele, founder of Emerge America, a nonprofit that trains women for political leadership. "We don't feel as qualified as men; we're not recruited in the same numbers; we feel turned off by the mechanics; we have persistent family barriers, and we don't have the same networks as men."

Those networks and social supports make a difference. Obama might not have been able to make his first runs for the Illinois statehouse and Congress without the stability of a two-income home and a wife who also took care of the kids. But according to the Joint Center for Political and Economic Studies, black women, especially since the 1970s, have traditionally had fewer of these support systems--and are more likely to be the single breadwinners in their household.

Lacking a Sense of Entitlement

What's more, Obama had been tagged for greatness from his earliest days as a student at Harvard Law School. Karen Bass, a congressional candidate who was the first black woman to lead the state assembly in California, didn't have that sense of destiny. Having spent over 20 years as an activist in her community, organizing voters, developing domestic and foreign public policy, educating elected officials, watching them term in and term out of office--her own qualifications as a candidate didn't spring to mind. "One person who was really instrumental in me running was my congressman, Diane Watson--who tapped me and told me that I had been in the community long enough, and that I had to go to Sacramento because there were no African-American women in the state legislature," she recalls. "And when someone like that calls on you, you respond."

Bass' case is not uncommon. Studies have shown that women win elections just as often as men--but it takes seven people to convince a woman to run, as opposed to a single fan for male politicians. "We are not set up with the same sense of entitlement," says Pressley. "Which is why a 19-year-old white male will challenge an incumbent and a woman of color who is the VP of a company, who serves on nine boards, has two advanced degrees and raised four children will say no. We never think we're ready. We never think we're good enough."

Flying Without a Net

The "persistent family barriers" Steele spoke of are also a contributing factor. Donna Edwards, a freshman congresswoman from Maryland who won her seat in 2008, says she could only contemplate running for office once her son headed to college, and "I didn't have to be the mom driving him around the beltway, going to different events and back and forth to school and work." Her decision to run for her first election came from a sense that incumbent Al Wynn wasn't right for her district. So on a quiet Good Friday, Edwards drove alone down to a filing center, wrote a check for $100 and "became a candidate for the 4th congressional district of Maryland," she recalls. "It's a pretty nontraditional pathway to Congress ... And I would never have done it with a small child."

Fundraising is even tougher for women representing communities of color that are less accustomed to handing money to candidates. "Oftentimes our communities are the beneficiaries of governmental goodwill," explains Yvette Clarke, who represents Brooklyn in the House of Representatives. "And the prospect of financing a government official, even in the political realm, is one that people haven't quite grabbed hold of yet."

Edwards was unique in that she became a darling of online progressive organizations like Act Blue and MoveOn, which raised tens of thousands of dollars for her attempt to defeat Wynn. "So many of us come to the table with big ideas, but we're not independently wealthy," she says. (In states like Maine and Arizona, which publicly finance state campaigns and restrict how much a candidate can raise from private sources, the rate of female political participation is much higher.)

Under the Media Microscope

And there is yet another layer to the glass ceiling for women, and particularly black women: the media. Erika Falk, a professor at Johns Hopkins University and author of the book Woman for President, demonstrates a strong and unsettling media bias stretching back to the first female candidates--running in the 19th century. According to her research, women are less frequently written about, and for fewer substantive issues (no matter how much they know about cap and trade). They are more often described using physical characteristics such as what they are wearing, and are more frequently referred to by their married names--such as "Mrs. Clinton" rather than "Sen. Clinton." "The trend lines are flat," Falk says. "When you consider the social changes that have gone on since 1872," she adds, "the fact that the press coverage [has] not improved is really astonishing."

These pervasive media habits serve to diminish women in the eyes of voters--and are rarely applied with such regularity to male candidates. "A woman's hair will make or break her candidacy for high office," says Maureen Bunyan, a longtime Washington journalist on the board of the International Women's Media Foundation.

Sure, John Edwards was briefly known as the "Breck Girl" for his $400 hair-care regime. But it was nothing compared to the hoopla over Clinton's pantsuits, which even spawned a debate question in the Democratic primary. And newly elected Sen. Scott Brown appeared semi-nude as a Playgirl centerfold--which did nothing to diminish his electoral chances. According to a recent Vanity Fair poll, 77 percent of women believed that a female candidate who had pulled the same stunt would have lost any hope of winning. (Strangely, only 56 percent of men thought so).

"The level of scrutiny is certainly more intense for women," says Pressley. "But everything in life is harder to do when you're a woman and certainly a woman of color and a progressive woman of color."

Another contributor to the problem is the evolution and portrayal of American politics as a blood sport. Rather than being a space for public policy to be implemented by reasonable actors, Washington and many state capitals are populated with verbs like "spar," "hammer," "slam" and "blast," which suggest anything but smart solutions for constituents--and punish women who jump into the fray. Elisabeth Gidengil of McGill University, who has researched racial and gender biases in politics says that "when politics is characterized or likened to arenas that we still associate with men, the not-so-subliminal message is that women don't really belong there."

Black women who are not seen as conciliatory sometimes get the short end of the stick. "Behavior that's seen as appropriately assertive [in men] is seen as inappropriately aggressive on the part of the female," says Gidengil. "This presents women candidates with a classic damned if you do, damned if you don't, dilemma." Black women struggle additionally with prevailing cultural perceptions about a black woman's "attitude." "I say what's on my mind, and I'm not going to not express my opinion or point of view because I'm the only girl in the room," says Moseley Braun, who was voted out of office by Republican Peter Fitzgerald in 1998. "And I paid the price for it."

Contributing to this dilemma, adds Bunyan, are other women--who, as the 2008 showdown between Hillary Clinton and Obama showed, are not always eager to favor gender in their voting decisions or speak up when women candidates are being treated unfairly by the media.

"I don't hear us resoundingly expressing our concerns about the way women candidates are portrayed, the misogynistic language of the right-wing radio talk shows," says Bunyan. "We haven't yet found a way to think and to talk about women who are well-educated, ambitious, accomplished and good citizens who want to be leaders in society."

Tune in to part three of this series tomorrow, when The Root looks at the black women who are really doing it--in races large and small across America. Read Part 1 here.

Dayo Olopade is Washington reporter for The Root. Follow her on Twitter.